2-(4-Acetylamino-phenoxy)-propionic acid methyl ester → 2-(4-Aminophenoxy)propanoic acid

HRID 638709Notes

Reaction equation

HRID 638709 reaction equation
C[O:2][C:3](=[O:17])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13]C(=O)C)=[CH:9][CH:8]=1)[CH3:5]>Cl>[NH2:13][C:10]1[CH:9]=[CH:8][C:7]([O:6][CH:4]([CH3:5])[C:3]([OH:17])=[O:2])=[CH:12][CH:11]=1

Participants

3

Reactant 1

HCID 549413982-(4-Acetylamino-phenoxy)-propionic acid methyl ester

Product 1

HCID 141969882-(4-Aminophenoxy)propanoic acidYield 98.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 2-(4-Acetylaminophenoxy)propionic acid methyl ester 16 (320 grams, 1.35 mol) in concentrated hydrochloric acid (8 liters) was refluxed for 48 hours. Excess concentrated hydrochloric acid was distilled off in vacuum and filtered hot. The mixture was cooled to 10° C., filtered and dried to give pure 17 (240 g, 81.7%) as a brown powder. The melting point was found to be 175-180° C.

Workup

  1. temperaturewas refluxed for 48 hours
  2. distillationExcess concentrated hydrochloric acid was distilled off in vacuum
  3. filtrationfiltered hot
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-c084b1472b4042d7afa28f58c30d85b8
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Reaction notes

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